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DE1289425B - Photosensitive copying material which, as photosensitive substance, contains at least one derivative of p-phenylenediamine which is diazotized on one side and has an alkoxy group in the m-position to the diazo group - Google Patents

Photosensitive copying material which, as photosensitive substance, contains at least one derivative of p-phenylenediamine which is diazotized on one side and has an alkoxy group in the m-position to the diazo group

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Publication number
DE1289425B
DE1289425B DEK56061A DEK0056061A DE1289425B DE 1289425 B DE1289425 B DE 1289425B DE K56061 A DEK56061 A DE K56061A DE K0056061 A DEK0056061 A DE K0056061A DE 1289425 B DE1289425 B DE 1289425B
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DE
Germany
Prior art keywords
group
parts
carbon atoms
derivative
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
DEK56061A
Other languages
German (de)
Inventor
Dr Herbert
Rauhut
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kalle GmbH and Co KG
Original Assignee
Kalle GmbH and Co KG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to NL297944D priority Critical patent/NL297944A/xx
Priority to DENDAT1249682D priority patent/DE1249682B/en
Priority to DENDAT1249683D priority patent/DE1249683B/en
Priority to DEK47829A priority patent/DE1226879B/en
Priority to NL63297944A priority patent/NL140344B/en
Priority to GB36951/63A priority patent/GB1001493A/en
Priority to CH1167663A priority patent/CH439960A/en
Priority to SE10384/63A priority patent/SE301420B/xx
Priority to US311220A priority patent/US3272630A/en
Priority to FR948777A priority patent/FR1375314A/en
Priority to BE651969A priority patent/BE651969A/xx
Priority to NL6413684A priority patent/NL6413684A/xx
Priority to SE14456/64A priority patent/SE327134B/xx
Priority to BE656466A priority patent/BE656466A/xx
Priority to CH1547764A priority patent/CH450912A/en
Priority to GB49039/64A priority patent/GB1062918A/en
Priority to FR997234A priority patent/FR87605E/en
Priority to NL646414808A priority patent/NL141657B/en
Priority to CH61265A priority patent/CH450913A/en
Priority to SE00573/65A priority patent/SE329331B/xx
Priority to US425921A priority patent/US3432301A/en
Priority to DEK56060A priority patent/DE1289736B/en
Application filed by Kalle GmbH and Co KG filed Critical Kalle GmbH and Co KG
Priority to DEK56061A priority patent/DE1289425B/en
Priority to NL666605723A priority patent/NL149294B/en
Priority to US547738A priority patent/US3462271A/en
Priority to DK231366AA priority patent/DK114170B/en
Priority to DK231666AA priority patent/DK116488B/en
Priority to ES0326361A priority patent/ES326361A1/en
Priority to AT427566A priority patent/AT269643B/en
Priority to US547721A priority patent/US3459551A/en
Priority to GB20201/66A priority patent/GB1122104A/en
Priority to NL6606212A priority patent/NL6606212A/xx
Priority to CH661366A priority patent/CH468024A/en
Priority to CH661466A priority patent/CH468025A/en
Priority to FR60505A priority patent/FR90130E/en
Priority to BE680701D priority patent/BE680701A/xx
Priority to SE06295/66A priority patent/SE340043B/xx
Priority to FI1196/66A priority patent/FI44335B/fi
Priority to GB20202/66A priority patent/GB1122249A/en
Priority to SE06294/66A priority patent/SE340042B/xx
Priority to FI1197/66A priority patent/FI44191B/fi
Publication of DE1289425B publication Critical patent/DE1289425B/en
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
    • B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • B01J29/061—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof containing metallic elements added to the zeolite
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G27/00—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation
    • C10G27/04—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G27/00—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation
    • C10G27/04—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen
    • C10G27/06—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen in the presence of alkaline solutions
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/52—Compositions containing diazo compounds as photosensitive substances
    • G03C1/54—Diazonium salts or diazo anhydrides

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyrrole Compounds (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)

Description

Gegenstand des Hauptpatents 1 226 X79 ist lichtempfindliches Kopiermaterial, das als lichtempfindliche Substanz mindestens ein Derivat des einseitig diazotierten p-Phenylendiamins mit einer Alkoxygruppe in m-Stellung zur Diazogruppe enthält, das dadurch gekennzeichnet ist daß das Derivat der allgemeinen Formel entspricht. in der R1 eine Alkylgruppe mit höchstens 4 Kohlenstoffatomen, R eine Alkylgruppe mit höchstens 4 Kohlenstoffatomen oder eine Aralkylgruppe mit höchstens 10 Kohlenstoffatomen ist oder R1 und R gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, eine heterocyclische Gruppe bilden, die einen oder mehrere Substituenten tragen kann, Z eine Alkoxygruppe. eine arylierte Alkoxygruppe oder eine Aryloxygruppe oder die Gruppe in der R und R, je eine Alkylgruppe mit höchstens 4 Kohlenstoffatomen sind oder gemeinsam mit dem Stickstoffatom, an das sie gebunden sind. eine heterocyclische Gruppe bilden, die einen oder mehrere SubstitLlenten tragen kann, X Wasserstoff, Halogen oder die Methylgruppe, Y das Anion einer Säure, n eine ganze Zahl von 1 bis 4 und kl gleich O oder 1 ist und in der die Summe 11 + In mindestens gleich 2 ist.The subject of the main patent 1 226 X79 is light-sensitive copying material which contains as light-sensitive substance at least one derivative of p-phenylenediamine diazotized on one side with an alkoxy group in the m-position to the diazo group, which is characterized in that the derivative of the general formula is equivalent to. in which R1 is an alkyl group with at most 4 carbon atoms, R is an alkyl group with at most 4 carbon atoms or an aralkyl group with at most 10 carbon atoms or R1 and R together with the nitrogen atom to which they are bonded form a heterocyclic group which has one or more substituents can carry, Z is an alkoxy group. an arylated alkoxy group or an aryloxy group or the group in which R and R, are each an alkyl group with a maximum of 4 carbon atoms or together with the nitrogen atom to which they are attached. form a heterocyclic group which can carry one or more substituents, X is hydrogen, halogen or the methyl group, Y is the anion of an acid, n is an integer from 1 to 4 and kl is 0 or 1 and in which the sum 11 + In is at least 2.

Gegenstand des Zusatzpatents 1 249 682 ist lichtempfindliches Diazotypie-Kopiermaterial, das gekennzeichnet ist durch ein einseitig diazotiertes p-Phenylendiaminderivat entsprechend der im Hauptpatent genannten allgemeinen Formel, in der aber Z eine Alkylmerkaptogruppe darstellt oder die Gruppe in der R, 3 Wasserstoff oder eine Hydroxyalkylgruppe mit höchstens 4 Kohlenstoffatomen und R1 eine Alkylgruppe oder Hydroxyalkylgruppe mit jeweils höchstens 4 Kohlenstoffatomen ist.The subject of additional patent 1 249 682 is light-sensitive diazotype copying material which is characterized by a p-phenylenediamine derivative diazotized on one side according to the general formula mentioned in the main patent, but in which Z represents an alkyl mercapto group or the group in which R, 3 is hydrogen or a hydroxyalkyl group with at most 4 carbon atoms and R1 is an alkyl group or hydroxyalkyl group with in each case at most 4 carbon atoms.

Gegenstand des Zusatzpatents 1 249 683 ist ein lichtempfindliches Diazotypie-Kopiermaterial, das als lichtempfindliche Substanz mindestens ein Derivat des einseitig diazotierten p-Phenylendiamins mit einer Alkoxygruppe in m-Stellung zur Diazogruppe enthält, wobei in diese Alkoxygruppe mindestens I Heteroatom in Form von Athergruppen oder tertiären Aminogruppen eingeführt ist, nach dem Hauptpatent. das dadurch gekennzeichnet ist, daß das Derivat der allgemeinen Formel entspricht in der R eine Alkylgruppe mit höchstens 4 Kohlenstoffatomen, R eine Alkylgruppe mit höchstens 4 Koillenstottatomen oder eine Aralkylgruppe mit höchstens 10 Kohlenstoffatomen ist oder R1 und R gemeinsam mit dem Stickstoffatom N an das sie gebunden sind. eine heterocyclische Gruppe bilden, die einen oder mehrere Substituenten tragen kann, und Z eine Alkoxygruppe. eine arylierte Alkoxygruppe. eine Aryloxygruppe, eine Alkylmerkaptogruppe. eine Arylmerkaptogruppe oder die Gruppe bedeutet, in der R. s Wasserstoff, eine Alkylgruppe mit höchstens 4 Kohlenstoffatomen, eine Hydroxyalkylgruppe mit höchstens 4 Kohlenstoffatomen, R.1 eine Alkylgruppe mit höchstens 4 Kohlenstoffatomen, eine Hydroxyalkylgruppe mit höchstens 4 Kohlenstoffatomen oder eine Aralkylgruppe mit höchstens 10 Kohlenstoffatomen darstellt oder R.1 und Rl gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, eine heterocyclische Gruppe bilden, die einen oder mehrere Substituenten tragen kann.The subject of the additional patent 1 249 683 is a light-sensitive diazotype copying material which contains as light-sensitive substance at least one derivative of the unilaterally diazotized p-phenylenediamine with an alkoxy group in the m-position to the diazo group, in this alkoxy group at least 1 heteroatom in the form of ether groups or tertiary groups Amino groups is introduced, according to the main patent. which is characterized in that the derivative of the general formula corresponds in which R is an alkyl group with a maximum of 4 carbon atoms, R is an alkyl group with a maximum of 4 Koillenstottatomen or an aralkyl group with a maximum of 10 carbon atoms or R1 and R together with the nitrogen atom N to which they are bonded. form a heterocyclic group which can carry one or more substituents, and Z is an alkoxy group. an arylated alkoxy group. an aryloxy group, an alkyl mercapto group. an aryl mercapto group or the group in which R. s denotes hydrogen, an alkyl group with at most 4 carbon atoms, a hydroxyalkyl group with at most 4 carbon atoms, R.1 an alkyl group with at most 4 carbon atoms, a hydroxyalkyl group with at most 4 carbon atoms or an aralkyl group with at most 10 carbon atoms or R. 1 and Rl together with the nitrogen atom to which they are attached form a heterocyclic group which can carry one or more substituents.

Gegenstand der vorliegenden Zusatzerfindung ist ein lichtempfindliches Kopiermaterial. das als lichtempfindliche Substanz mindestens ein Derivat des einseitig diazotierten p-Phenylendiamins mit einer Alkoxygruppe in m-Stellung zur Diazogruppe enthält, wobei an die Alkoxygruppe endständig eine Aminogruppe gebunden ist, nach Patent 1 226 879 und dessen Zusatzpatenten 1 249 682 und 1 249 683, und ist dadurch gekennzeichnet, daß das Derivat der Formel entspricht, in der R1 eine Alkylgruppe mit höchstens 4 Kohlenstoffatomen, R eine Alkylgruppe mit höchstens 4 Kohlenstoffatomen oder eine Aralkylgruppe mit höchstens 10 Kohlenstoffatomen bedeutet oder R1 und R2 gemeinsam mit dem Stickstoffatom N, an das sie gebunden sind, eine heterocyclische Gruppe bilden, die einen oder mehrere Substituenten tragen kann, Q einen wenigstens 2 Kohlenstoffatome enthaltenden Alkylen- oder Itydroxynikylenrest, Ra und RI Alkyl oder Hydroxyalkyl bedeuten oder R, l und Ri gemeinsam mit dem Stickstoffatom an das sie gebunden sind. einen gegebenenfalls substituierten hetelocyclischen Rest bilden, R, Alkyl oder Aralkyl X ein Wasserstoff- oder Halogenatom oder eine Alkyl- oder Alkoxygruppe. Y und Y, je das Anion einer Säure bedeuten.The subject of the present additional invention is a photosensitive copying material. which contains as a light-sensitive substance at least one derivative of p-phenylenediamine diazotized on one side with an alkoxy group in the m-position to the diazo group, an amino group being attached to the terminal alkoxy group, according to patent 1,226,879 and its additional patents 1,249,682 and 1,249,683, and is characterized in that the derivative of the formula corresponds, in which R1 is an alkyl group with at most 4 carbon atoms, R is an alkyl group with at most 4 carbon atoms or an aralkyl group with at most 10 carbon atoms or R1 and R2 together with the nitrogen atom N to which they are bonded form a heterocyclic group, the one or can carry several substituents, Q is an alkylene or Itydroxynikylenrest containing at least 2 carbon atoms, Ra and RI are alkyl or hydroxyalkyl or R, l and Ri together with the nitrogen atom to which they are bonded. form an optionally substituted heterocyclic radical, R, alkyl or aralkyl, X a hydrogen or halogen atom or an alkyl or alkoxy group. Y and Y, each represent the anion of an acid.

Die der vorstehend angegebenen allgemeinen Formel entsprechenden p-Aminobenzoldiazoniumsalze weisen hohe Lichtempfindlichkeit und ausgezeichnete Stabilität auf. Ihr Aufziehvermögen ist besser als das der p-Aminobenzoldiazoverbindungen, die das Kopiermaterial nach dem Hauptpatent und den oben angeft ihrten Zusatzpatenten kennzeichnen. Those corresponding to the general formula given above p-Aminobenzenediazonium salts have high photosensitivity and excellent Stability on. Their absorption capacity is better than that of the p-aminobenzene diazo compounds, the copy material according to the main patent and the additional patents attached above mark.

Den Kopiermaterialien, die Gegenstand dieser älteren Erfindungen sind. kommt das erfindungsgefäße Kopiermaterial mindestens gleich an Lagerfähigkeit. The copy materials that were the subject of these older inventions are. the copier material according to the invention has at least the same shelf life.

Die p-Aminobenzoldiazoverbindungen entsprechend der vorstehend angegebenen allgemeinen Formcl haben noch keinen Eingang in die Literatur gefunden. Man erhält sie nach Verfahren. die in der Literatur oder im Hauptpatent bzw. in den Zusatzpatenten beschrieben sind. Praktisch alle in diesen Patenten erwähnten p-tertiär-Amino-nitrobenzole mit einer tertiären Aminogruppe in der m-ständigen Athergruppe sind mit z. B. Alkyl- bzw. Aralkylhalogeniden oder Dialkylsulfaten nach gebräuchlichen Methoden in die quartäre Form überführbar Die lDberführung dieser quaternierten Verbindungen in Diazoverbindungen erfolgt ohne Schwierigkeiten. Die Abscheidung der Diazoverbindung erfolgt wie bekann in Form ihrer Metallhalogeniddoppelsalze oder auch auf andere , dem Fachmann bekannte Weise. The p-aminobenzenediazo compounds according to those given above general forms have not yet found their way into the literature. You get them according to procedure. those in the literature or in the main patent or in the additional patents are described. Virtually all of the p-tertiary-amino-nitrobenzenes mentioned in these patents with a tertiary amino group in the m-position ether group with z. B. alkyl or aralkyl halides or dialkyl sulfates by customary methods in the Quaternary form convertible The conversion of these quaternized compounds into Diazo compounds occur without difficulty. The deposition of the diazo compound takes place as is known in the form of their metal halide double salts or also to others manner known to the person skilled in the art.

In der Zeichnung sind die Formeln einiger Diazoverbindungen aufgeführt, durch die das erfindungsgemäße Kopiermaterial gekennzeichnet ist. In den folgenden Beispielen wird die Herstellung einiger von ihnen beschrieben. The drawing shows the formulas of some diazo compounds, by which the copying material according to the invention is characterized. In the following Examples describe the preparation of some of them.

Beispiel 1 Ein in der Diazotypie übliches Lichtpausrohpapier, das einseitig mit einem Vorstrich aus kolloidaler Kieselsäure und Polyvinylacetat versehen ist, wird auf der vorbestrichenen Oberfläche mit einer Lösung bestrichen, die in 100 Volumteilen Wasser 3,5 Gewichtsteile Zitronensäure, 3,5 Gewichtsteile Borsäure, 5,0 Gewichtsteile Thioharnstoff. Example 1 A blueprint base paper customary in the diazotype which Provided on one side with a primer made of colloidal silica and polyvinyl acetate is, is coated on the pre-painted surface with a solution that is in 100 parts by volume of water 3.5 parts by weight of citric acid, 3.5 parts by weight of boric acid, 5.0 parts by weight thiourea.

1,2 Gewichtsteile 3. 5-Dioxy4-brombenzoesäureamid, 2,4 Gewichtsteile der Diazoverbindung aus Triäthyl-11-(5-amino-2-pyrrolidinophenoxyäthyl)- ammoniumchlorid in Fonn des Zinkchloriddoppelsalzes enthält, und dann getrocknet. 1.2 parts by weight 3. 5-Dioxy4-bromobenzoic acid amide, 2.4 parts by weight the diazo compound from triethyl-11- (5-amino-2-pyrrolidinophenoxyethyl) ammonium chloride in the form of zinc chloride double salt, and then dried.

Wird das nach vorstehenden Anga°% ensibilisierte Kopierpapier unter einer transparenten Vorlage belichtet und dann mit Ammoniakdampf entwickelt, erhält man rote Bilder auf weißem Grund. If the copy paper that has been sensitized according to the above information is placed under exposed to a transparent original and then developed with ammonia vapor man red pictures on a white background.

Die Diazoverbindung mit der Formel 1 wurde wie folgt hergestellt: 145 Gewichtsteile 2-Chlor-5-nitrophenol werden in 400 Volumteilen Methylglykol und 220 Volumteilen Athylenbromid gelöst und unter Rühren zum Sieden erhitzt. Unter Rückfluß wird eine Lösung von 24 Gewichtsteilen Natriumhydroxyd in 250 Volumteilen Wasser innerhalb von 3 Stunden in die methylalkoholische Lösung eingetropft. Nach 2stündigem Nachrühren unter Rückfluß wird das Reaktionsgemisch warm abgesaugt. das Filtrat im Vakuum zur Trockne eingeengt und der Rückstand mit Wasser behandelt. abgesaugt und getrocknet. Ausbeute 165 Gewichtsteile xom Schmelzpunkt 71 bis 73 C. The diazo compound of Formula 1 was prepared as follows: 145 parts by weight of 2-chloro-5-nitrophenol are in 400 parts by volume of methyl glycol and Dissolved 220 parts by volume of ethylene bromide and heated to boiling with stirring. Under A solution of 24 parts by weight of sodium hydroxide in 250 parts by volume is refluxed Water within 3 hours into the methyl alcoholic solution was added dropwise. To After stirring for 2 hours under reflux, the reaction mixture is filtered off with suction while warm. the The filtrate was concentrated to dryness in vacuo and the residue was treated with water. vacuumed and dried. Yield 165 parts by weight from melting point 71 to 73 C.

3 () 5Gewiclltsteiledes2-Chlor-5-nitrophenyl-l.-brom-. ithyltitllers werden mit 385 Gewichtsteilen wasserfreiem Diäthylamin und 60 Volumteilen Wasser unter Rühren zum Sieden erhitzt. Nach 2stiindigem Sieden wird das Reaktionsgemisch auf Eiswasser gegossen. abgesaugt und gründlich mit Eiswasser gewaschen. Die erhaltenen 395 Gewichtsteile Umsetzungsprodukt werden noch feucht mit 450 Volumteilen Pyrrolidin und 30 Volumteilen Wasser übergossen und unter Rühren zum Sieden erhitzt. Nach etwa 3stündigem Rühren des Gemisches unter Riickfluß werden 180 Volumteile Pyrrolidin abdestillicrt. Der Rückstand wird auf Eiswasser gegossen. abgesaugt und gründlich mit Wasser gewaschen. 3 () 5 parts by weight of the 2-chloro-5-nitrophenyl-l.-bromo-. ithyltitllers with 385 parts by weight of anhydrous diethylamine and 60 parts by volume of water heated to boiling with stirring. After boiling for 2 hours, the reaction mixture becomes poured onto ice water. Aspirated and washed thoroughly with ice water. The received 395 parts by weight of reaction product are still moist with 450 parts by volume of pyrrolidine and 30 parts by volume of water poured over it and heated to the boil while stirring. After about After stirring the mixture for 3 hours under reflux, 180 parts by volume of pyrrolidine are added distilled off. The residue is poured onto ice water. vacuumed and thoroughly washed with water.

Ausbeute an 5-Nitro-2-pyrrolidinopl1enyl-l ;-diäthylaminoäthyläther 325 Gewichtsteile vom Schmelzpunkt 39 C. nach Umkristallisieren aus Leichtbenzin wird der Schmelzpunkt 42 C erhalten.Yield of 5-nitro-2-pyrrolidinopl1enyl-l; -diethylaminoethyl ether 325 parts by weight with a melting point of 39 C. after recrystallization from light gasoline the melting point 42 C is obtained.

160 Gewichtsteile 5-Nitro-2- pyrrolidinophenylsi-disithylaminoäther werden in 100 Volumteilen Aceton gelöst, die Lösung wird unter Rühren zum Sieden erhitzt und tropfenweise mit 75 Volumteilen Athyljodid versetzt. Nach 1 stündigem Nachrühren unter Rückfluß wird das Reaktionsgemisch abgekühlt. abgesaugt, mit Aceton digeriert und getrocknet. 160 parts by weight of 5-nitro-2-pyrrolidinophenylsi-disithylaminoether are dissolved in 100 parts by volume of acetone, the solution is brought to the boil while stirring heated and treated dropwise with 75 parts by volume of ethyl iodide. After 1 hour The reaction mixture is then cooled under reflux. suctioned off with acetone digested and dried.

Ausbeute 95 g vom Schmelzpunkt 197 C.Yield 95 g with a melting point of 197 C.

30 Gewichtsteile des so hergestellten Triiithyl-P-(S-nitro- 2-pyrrojidinophenoxyäthyl)-ammoniumjodids werden in 200 Volumteilen Methanol in Gegenwart eines aktiven Nickelkatalysators mit Wasserstoff hydriert. Die entstandene Aminoverbindung wird nach Abfiltrieren des Katalysators und Abdampfen des Lösungsmittels ohne Reinigung in 80 Volumteilen Wasser und 20 Volumteilen Salzsäure gelöst und bei 0 bis 10 C mit 33 Volumteilen 2 n-Natriumnitritlösung diazotiert. Nach Verdünnen des Diazotiergemisches mit 100 Volumteilen Wasser wird das Gemisch über Kohle filtriert, mit einer wässerigen Lösung von 15 Gewichtsteilen Zinkchlorid versetzt und mit Kochsalz ausgesalzen. 30 parts by weight of the triithyl-P- (S-nitro-2-pyrrojidinophenoxyethyl) ammonium iodide thus prepared are in 200 parts by volume of methanol in the presence of an active nickel catalyst hydrogenated with hydrogen. The amino compound formed is filtered off of the catalyst and evaporation of the solvent without purification in 80 parts by volume Dissolved water and 20 parts by volume of hydrochloric acid and at 0 to 10 C with 33 parts by volume 2 n-sodium nitrite solution diazotized. After diluting the diazotization mixture with 100 Parts by volume of water, the mixture is filtered through charcoal with an aqueous solution mixed with 15 parts by weight of zinc chloride and salted out with table salt.

Ausbeute 11 Gewichtsteile der Verbindung der Formel 1 nach Um lösten aus Wasser-Kochsalz-Lösung. Yield 11 parts by weight of the compound of formula 1 after order solved from water-common salt solution.

Beispiel 2 Ein in der Diazotypie übliches Lichtpausrohpapier, das einseitig mit einem Vorstrich aus kolloidaler Kieselsäure und Polyvinylacetat versehen ist, wird auf der vorbestrichenen Oberfläche mit einer Lösung bestrichen, die in 100 Volumteilen Wasser 4,0 Gewichtsteile Zitronensäure, 5,0 Gewichtsteile Thioharnstoff, 3,0 Gewichtsteile Aluminiumsulfat, 3,5 Gewichtsteile 1,3,6- naphthalintrisulfosaures Natrium, 2,4 Gewichtsteile 2,7-dihydroxynaphthalin-3,6-disulfonsaures Natrium, 1,0 Gewichtsteil Zinkchlorid, 2.3 Gewichtsteile der Diazoverbindung aus Triäthyl-,-(5-amino-2-pyrrolidinophenoxy-j?-hydroxypropyl)-ammoniumchlorid in Form des Zinkchloriddoppelsalzes (Formel 3) enthält. und dann getrocknet. Example 2 A blueprint base paper customary in the diazotype which Provided on one side with a primer made of colloidal silica and polyvinyl acetate is, is coated on the pre-painted surface with a solution that is in 100 parts by volume of water, 4.0 parts by weight of citric acid, 5.0 parts by weight of thiourea, 3.0 parts by weight of aluminum sulfate, 3.5 parts by weight of 1,3,6-naphthalenetrisulfonic acid Sodium, 2.4 parts by weight of 2,7-dihydroxynaphthalene-3,6-disulfonic acid sodium, 1.0 Part by weight zinc chloride, 2.3 parts by weight of the diazo compound from triethyl - (5-amino-2-pyrrolidinophenoxy-j? -hydroxypropyl) ammonium chloride in Contains form of the zinc chloride double salt (formula 3). and then dried.

Das Kopierpapier ist von sehr guter Lagerfähigkeit. Wird das nach vorstehenden Angaben sensibilisierte Kopierpapier unter einer transparenten Vorlage bildmäßig belichtet und dann mit Ammoniakdampf entwickelt, erhält man blaue Bilder auf weißem Grund. The copy paper has a very good shelf life. Will that after above, sensitized copy paper under a transparent template exposed imagewise and then developed with ammonia vapor, blue images are obtained on a white background.

Die verwendete Diazoverbindung mit der Formel 3 wird analog der für die im Beispiel 1 beschriebene Diazoverbindung angegebenen Methode hergestellt. The diazo compound used with the formula 3 is analogous to that for the method described in Example 1 diazo compound prepared.

Das 2-Chlor-5-nitrophenol wird jedoch hier mit Epichlorhydrin statt mit Athylenbromid umgesetzt.The 2-chloro-5-nitrophenol, however, is held here with epichlorohydrin implemented with ethylene bromide.

Die in den Beispielen angeführten Volum- und Gewichtsteile stehen im Verhältnis zueinander wie Kubikzentimeter zu Gramm. The parts by volume and weight given in the examples are available in relation to each other like cubic centimeters to grams.

Claims (1)

Patentanspruch: Lichtempfindliches Kopiermaterial, das als lichtempfindliche Substanz mindestens ein Derivat des einseitig diazotierten p-Phenylendiamins mit einer Alkoxygruppe in m-Stellung zur Diazogruppe enthält, wobei an die Alkoxygruppe endständig eine Aminogruppe gebunden ist. nach Patent 1 226 879 und dessen Zusatzpatenten 1 249 682 und 1 249 683, d a d u r c h g e k e n n -z e i c h n e t . daß dieses Derivat der Formel entspricht, in der Rl eine Alkylgruppe mit höchstens 4 Kohlenstoffatomen, R2 eine Alkylgruppe mit höchstens 4 Kohlenstoffatomen oder eine Aralkylgruppe mit höchstens 10 Kohlenstoffatomen bedeutet oder R1 und R, gemeinsam mit dem Stickstoffatom N, an das sie gebunden sind. eine heterocyclische Gruppe bilden. die einen oder mehrere Substituenten tragen kann.Claim: Photosensitive copying material which contains as photosensitive substance at least one derivative of p-phenylenediamine diazotized on one side with an alkoxy group in the m-position to the diazo group, an amino group being terminally bonded to the alkoxy group. according to patent 1,226,879 and its additional patents 1,249,682 and 1,249,683, marked thereby. that this derivative of the formula in which R1 is an alkyl group with at most 4 carbon atoms, R2 is an alkyl group with at most 4 carbon atoms or an aralkyl group with at most 10 carbon atoms, or R1 and R together with the nitrogen atom N to which they are bonded. form a heterocyclic group. which can carry one or more substituents. Q einen wenigstens zwei Kohlenstoffatome enthaltenden Alkylen- oder Hydroxyalkylenrest, R. 3 und R Alkyl oder Hydroxyalkyl bedeuten oder Ri und R1 gemeinsam mit dem Stickstsffatom. an das sie gebunden sind, einen gegebenenfalls substituierten heterocyclischen Rest bilden. R, Alkyl oder Aralkyl. X ein Wasserstoff- oder Halogenatom oder eine Alkyl- oder Alkoxygruppe.Q is an alkylene or alkylene containing at least two carbon atoms Hydroxyalkylene radical, R. 3 and R denote alkyl or hydroxyalkyl or Ri and R1 together with the nitrogen atom. to which they are bound, an optionally substituted one form heterocyclic radical. R, alkyl or aralkyl. X is a hydrogen or halogen atom or an alkyl or alkoxy group. Yt und Y je das Anion einer Säure bedeuten.Yt and Y each represent the anion of an acid.
DEK56061A 1962-09-26 1965-05-08 Photosensitive copying material which, as photosensitive substance, contains at least one derivative of p-phenylenediamine which is diazotized on one side and has an alkoxy group in the m-position to the diazo group Pending DE1289425B (en)

Priority Applications (41)

Application Number Priority Date Filing Date Title
NL297944D NL297944A (en) 1962-09-26
DENDAT1249682D DE1249682B (en) 1962-09-26 Photosensitive copying material with p-phenylenediamine derivative diazotized on one side as a photosensitive substance
DENDAT1249683D DE1249683B (en) 1962-09-26 Photosensitive copying material with p-phenylenediamine derivative diazotized on one side as a photosensitive substance
DEK47829A DE1226879B (en) 1962-09-26 1962-09-26 Light-sensitive copying material with p-phenylenediamine derivative diazotized on one side as a light-sensitive substance
NL63297944A NL140344B (en) 1962-09-26 1963-09-16 SENSITIVE COPIER.
GB36951/63A GB1001493A (en) 1962-09-26 1963-09-19 Diazotype copying material
CH1167663A CH439960A (en) 1962-09-26 1963-09-23 Photosensitive copying material
SE10384/63A SE301420B (en) 1962-09-26 1963-09-23
US311220A US3272630A (en) 1962-09-26 1963-09-24 Light-sensitive reproduction material containing unilaterally diazotized p-phenylene-diamine derivatives as the light sensitive substance
FR948777A FR1375314A (en) 1962-09-26 1963-09-26 Single-function diazotized light-sensitive derivative of p-phenylenediamine, method of preparation, and light-sensitive reproductive material containing this derivative
BE651969A BE651969A (en) 1962-09-26 1964-08-18
NL6413684A NL6413684A (en) 1962-09-26 1964-11-25
SE14456/64A SE327134B (en) 1962-09-26 1964-11-30
BE656466A BE656466A (en) 1962-09-26 1964-11-30
CH1547764A CH450912A (en) 1962-09-26 1964-12-01 Photosensitive copying material with p-phenylenediamine derivative diazotized on one side as a photosensitive substance
GB49039/64A GB1062918A (en) 1962-09-26 1964-12-02 Novel diazonium compounds and diazotype copying material
FR997234A FR87605E (en) 1962-09-26 1964-12-03 Single function diazotized light-sensitive derivative of p-phenylenediamine, method of preparation and light-sensitive reproductive material containing this derivative
NL646414808A NL141657B (en) 1962-09-26 1964-12-18 LIGHT-SENSITIVE COPY MATERIAL WITH A SIDE DIASOTATED P-PHENYLENE DIAMINE DERIVATIVE AS A LIGHT-SENSITIVE FABRIC.
SE00573/65A SE329331B (en) 1962-09-26 1965-01-15
US425921A US3432301A (en) 1962-09-26 1965-01-15 Reproduction material
CH61265A CH450913A (en) 1962-09-26 1965-01-15 Photosensitive copying material with p-phenylenediamine derivative diazotized on one side as a photosensitive substance
DEK56060A DE1289736B (en) 1962-09-26 1965-05-08 Photosensitive copying material which contains as photosensitive substance at least one derivative of p-phenylenediamine which is diazotized on one side and has an alkoxy group in the m-position to the diazo group
DEK56061A DE1289425B (en) 1962-09-26 1965-05-08 Photosensitive copying material which, as photosensitive substance, contains at least one derivative of p-phenylenediamine which is diazotized on one side and has an alkoxy group in the m-position to the diazo group
NL666605723A NL149294B (en) 1962-09-26 1966-04-28 LIGHT-SENSITIVE COPY MATERIAL CONTAINING AS A PHOTOSENSITIVE SUBSTANCE A SIDE DIASOTATED P-PHENYLENE DIAMINE DERIVATIVE.
US547738A US3462271A (en) 1962-09-26 1966-05-05 Diazotype material
DK231366AA DK114170B (en) 1962-09-26 1966-05-05 Diazotype material containing, as photosensitive substance, one or more p-aminobenzenediazo compounds.
DK231666AA DK116488B (en) 1962-09-26 1966-05-05 Diazotype material containing, as photosensitive substance, one or more p-aminobenzenediazo compounds.
ES0326361A ES326361A1 (en) 1965-05-08 1966-05-05 Improvements introduced in copiative material of the type containing diazoted p-fenilendiamine derivatives. (Machine-translation by Google Translate, not legally binding)
AT427566A AT269643B (en) 1965-05-08 1966-05-05 Photosensitive copying material
US547721A US3459551A (en) 1962-09-26 1966-05-05 Diazotype material
GB20201/66A GB1122104A (en) 1962-09-26 1966-05-06 Novel diazo compounds and diazotype copying material
NL6606212A NL6606212A (en) 1962-09-26 1966-05-06
CH661366A CH468024A (en) 1962-09-26 1966-05-06 Photosensitive copying material with p-phenylenediamine derivative diazotized on one side as a photosensitive substance
CH661466A CH468025A (en) 1962-09-26 1966-05-06 Photosensitive copying material with p-phenylenediamine derivative diazotized on one side as a photosensitive substance
FR60505A FR90130E (en) 1962-09-26 1966-05-06 Light-sensitive derivative of diazotized p-phenylenediamine in a single function, method of preparation, and light-sensitive reproductive material containing this derivative
BE680701D BE680701A (en) 1962-09-26 1966-05-06
SE06295/66A SE340043B (en) 1962-09-26 1966-05-06
FI1196/66A FI44335B (en) 1962-09-26 1966-05-06
GB20202/66A GB1122249A (en) 1962-09-26 1966-05-06 Novel diazo compounds and diazotype copying material
SE06294/66A SE340042B (en) 1962-09-26 1966-05-06
FI1197/66A FI44191B (en) 1962-09-26 1966-05-06

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DEK47829A DE1226879B (en) 1962-09-26 1962-09-26 Light-sensitive copying material with p-phenylenediamine derivative diazotized on one side as a light-sensitive substance
DEK0051523 1963-12-03
DEK0051880 1964-01-18
DEK56061A DE1289425B (en) 1962-09-26 1965-05-08 Photosensitive copying material which, as photosensitive substance, contains at least one derivative of p-phenylenediamine which is diazotized on one side and has an alkoxy group in the m-position to the diazo group
DEK56060A DE1289736B (en) 1962-09-26 1965-05-08 Photosensitive copying material which contains as photosensitive substance at least one derivative of p-phenylenediamine which is diazotized on one side and has an alkoxy group in the m-position to the diazo group

Publications (1)

Publication Number Publication Date
DE1289425B true DE1289425B (en) 1969-02-13

Family

ID=27512136

Family Applications (5)

Application Number Title Priority Date Filing Date
DENDAT1249682D Pending DE1249682B (en) 1962-09-26 Photosensitive copying material with p-phenylenediamine derivative diazotized on one side as a photosensitive substance
DENDAT1249683D Pending DE1249683B (en) 1962-09-26 Photosensitive copying material with p-phenylenediamine derivative diazotized on one side as a photosensitive substance
DEK47829A Pending DE1226879B (en) 1962-09-26 1962-09-26 Light-sensitive copying material with p-phenylenediamine derivative diazotized on one side as a light-sensitive substance
DEK56061A Pending DE1289425B (en) 1962-09-26 1965-05-08 Photosensitive copying material which, as photosensitive substance, contains at least one derivative of p-phenylenediamine which is diazotized on one side and has an alkoxy group in the m-position to the diazo group
DEK56060A Pending DE1289736B (en) 1962-09-26 1965-05-08 Photosensitive copying material which contains as photosensitive substance at least one derivative of p-phenylenediamine which is diazotized on one side and has an alkoxy group in the m-position to the diazo group

Family Applications Before (3)

Application Number Title Priority Date Filing Date
DENDAT1249682D Pending DE1249682B (en) 1962-09-26 Photosensitive copying material with p-phenylenediamine derivative diazotized on one side as a photosensitive substance
DENDAT1249683D Pending DE1249683B (en) 1962-09-26 Photosensitive copying material with p-phenylenediamine derivative diazotized on one side as a photosensitive substance
DEK47829A Pending DE1226879B (en) 1962-09-26 1962-09-26 Light-sensitive copying material with p-phenylenediamine derivative diazotized on one side as a light-sensitive substance

Family Applications After (1)

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DEK56060A Pending DE1289736B (en) 1962-09-26 1965-05-08 Photosensitive copying material which contains as photosensitive substance at least one derivative of p-phenylenediamine which is diazotized on one side and has an alkoxy group in the m-position to the diazo group

Country Status (9)

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US (4) US3272630A (en)
BE (3) BE651969A (en)
CH (3) CH439960A (en)
DE (5) DE1226879B (en)
DK (2) DK114170B (en)
FI (2) FI44335B (en)
GB (4) GB1001493A (en)
NL (6) NL140344B (en)
SE (5) SE301420B (en)

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DE1249682B (en) * 1962-09-26 1967-09-07 Kalle Aktiengesellschaft, Wies baden-Biebrich Photosensitive copying material with p-phenylenediamine derivative diazotized on one side as a photosensitive substance
US3379531A (en) * 1965-03-30 1968-04-23 Gen Aniline & Film Corp Two-component heat developing diazotypes
DE1597621A1 (en) * 1966-08-26 1970-06-25 Ricoh Kk Diazotype copy material
DE1793342C3 (en) * 1968-09-03 1979-05-23 Hoechst Ag, 6000 Frankfurt Fluorine-containing benzene diazonium compounds and their use in diazotype material
JPS5115858B2 (en) * 1972-04-17 1976-05-20
FR2400221A1 (en) * 1977-08-09 1979-03-09 Kodak Pathe PHOTOSENSITIVE DIAZONIUM COMPOUND USEFUL, IN PARTICULAR, FOR PREPARING LITHOGRAPHIC PRINTING BOARDS, PROCESS FOR PREPARING THIS COMPOUND AND PLATE PRESENSITIZED WITH THIS COMPOUND
CH661501A5 (en) * 1982-01-26 1987-07-31 Oreal COMPOUNDS DERIVATIVE FROM AMINO-3 PROPANOL-2 FOR USE IN DYEING HAIR, PREPARATION METHOD THEREOF, DYE COMPOSITION CONTAINING THE SAME, AND HAIR DYEING METHOD THEREOF.
EP1429771B1 (en) * 2001-08-30 2009-08-12 ChemoCentryx Inc Bicyclic compounds as inhibitors of chemokine binding to us28
DE102013220789A1 (en) * 2013-10-15 2015-04-16 Henkel Ag & Co. Kgaa Antiperspirant cosmetic products containing aromatic sulfonic acids

Citations (1)

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Publication number Priority date Publication date Assignee Title
DE1117387B (en) * 1960-03-04 1961-11-16 Kalle Ag Process for the production of duplicates with one-component diazotype layers

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US2529464A (en) * 1946-09-23 1950-11-07 Gen Aniline & Film Corp Diazotype composition containing n-hydroxyethyl-m-toluidine-p-diazos
US2552354A (en) * 1947-04-16 1951-05-08 Gen Aniline & Film Corp Diazotype layers containing diazos of n-(2-hydroxypropyl)-phenylenediamines
BE629326A (en) * 1962-03-09
DE1249682B (en) * 1962-09-26 1967-09-07 Kalle Aktiengesellschaft, Wies baden-Biebrich Photosensitive copying material with p-phenylenediamine derivative diazotized on one side as a photosensitive substance
DE1255486C2 (en) * 1963-09-14 1973-04-19 Kalle Ag Two component diazotype material
US3281246A (en) * 1964-11-30 1966-10-25 Keuffel & Esser Co Diazotype reproduction material

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1117387B (en) * 1960-03-04 1961-11-16 Kalle Ag Process for the production of duplicates with one-component diazotype layers

Also Published As

Publication number Publication date
CH439960A (en) 1967-07-15
DK114170B (en) 1969-06-02
CH468024A (en) 1969-01-31
GB1001493A (en) 1965-08-18
NL6606212A (en) 1966-11-10
SE340042B (en) 1971-11-01
NL141657B (en) 1974-03-15
BE651969A (en) 1965-02-18
GB1122249A (en) 1968-07-31
NL297944A (en)
US3462271A (en) 1969-08-19
NL6605723A (en) 1966-11-10
FI44191B (en) 1971-06-01
GB1122104A (en) 1968-07-31
DE1226879B (en) 1966-10-13
SE340043B (en) 1971-11-01
NL6414808A (en) 1965-07-19
DK116488B (en) 1970-01-12
DE1249683B (en) 1967-09-07
BE680701A (en) 1966-11-07
BE656466A (en) 1965-05-31
NL149294B (en) 1976-04-15
CH468025A (en) 1969-01-31
DE1289736B (en) 1969-02-20
FI44335B (en) 1971-06-30
DE1249682B (en) 1967-09-07
US3459551A (en) 1969-08-05
NL140344B (en) 1973-11-15
US3272630A (en) 1966-09-13
NL6413684A (en) 1965-11-25
SE329331B (en) 1970-10-05
SE327134B (en) 1970-08-10
US3432301A (en) 1969-03-11
GB1062918A (en) 1967-03-22
SE301420B (en) 1968-06-04

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